I moderated a panel today at Gather on the topic of “Work”. We had representatives from different types of work: self-employed, salaried employee, startup, and investor. As moderator, my role wasn’t to share my opinions. Fortunately, on the Internet I’m also blogger, and my role as a blogger is to share my opinions. So: opinion follows.

The whole concept of “work” is fraught. We treated it as “how you make your money”, but that’s a concept that comes with a pile of baggage. If I make money from a lot of things (one panelist had her IT business, her music, and her writing all contributing) then which, all, or none of those are my “work”? Our language opposes “work” with “play”, but what if I like what I do? If I volunteer, is that work? If my partner earns money and I contribute my labour to upkeep of the family and house, is that “work”? Each of those is a set of dissertations and an argument waiting to happen.

There are types of “how I earn my money” work that we didn’t cover. For example, indie business is a thing and conferences like xoxo share role models and techniques. My take on indie is that it’s “you can make something, sell it, and never want to yield ownership or control over your work”. Indie doesn’t mean small, it means “organically grown”. The new capital, marketing, payment, and fulfilment systems created by new technology have enabled a lot of new businesses to start. We didn’t talk about them.

And then there’s unemployment. My role model when I was a child had been to university, moved into his parents’ home to look after them as they aged, stayed largely unemployed after they died, and had a rich intellectual and social life. Most unemployed people didn’t choose to be unemployed, and unemployment comes with restrictions, stigma, and challenges, but it’s a financial model and lifestyle that is an option for some people.

I alluded to Rich Dad, Poor Dad. It’s one of the terrible “how to get rich!” books that fill business shelves, but the bit that stuck with me was the breakdown of work into contracting, employed for someone else, employer, and investor. The bit I failed adequately to tease out in the panel is the idea that each has positives and negatives. Rough summary follows:

Contracting gives you great flexibility because you can dial up or down your hours, but you’ll find yourself doing a lot of extra work like finding and billing clients and the feast-famine nature of the business makes it very uncertain. The money you make is based on the hours you work.

Working for someone else gives you stability and predictable income, as well as possible training or other perks from your employer, and significantly it lets you do what you’re good at (you can be a designer without having to be sales, finance, etc. too). However, you lose autonomy and ultimately you’re working to make someone else rich.

Starting your own company gives you leveraged income because you can employ others and profit off their labour, as well as control over what your company builds, but your job becomes to run the business so you’ll need to enjoy that and get good at it. (the E-Myth book talks about this: if you like baking and start a bakery, your job is now to run a bakery not to bake)

Investing risks your income, but lets you leverage other people who started their own company. It’s not always an option for people in the “just kick $10k into someone’s project” sense.

Although startup people (like me) drink the kool-aid and sing the song of how wonderful startup life is, that life is not right for everyone. If you’re not comfortable with risk, if you want stability in your life, if you thrive in the presence of structure and process, then you’re probably not ready for startup life. And there’s a certain amount of “I’m going home and that’s ok” with jobs at corporates, which is an emotional distance between work and home that’s harder to attain in a smaller environment where the problems and opportunities are so much nearer and the work correspondingly so much harder to compartmentalise.

There’s much more to say. If you want, you can tell me what I else missed on Twitter. Stay awesome!